Li et al.
IR (KBr, ⁄ cm): 3297, 3202 (mNH), 1656 (tC=O), 1605, 1531, 1493
(tC=C), 1324, 1173 (tC-N); EI-MS: m ⁄ z 686.4 [M+H]. C27H17I2N3O3
(684.94).
7.74–7.77 (m, 5H, Ar-H), 7.70 (d, 2H, J = 1.8 Hz, Ar-H); IR
(KBr, ⁄ cm): 3335, 3221 (mNH), 1653 (tC=O), 1604, 1508, 1408 (tC=C),
1314, 1179 (tC-N); EI-MS: m ⁄ z 464.5 [M+H]. C27H21N5O3 (463.16).
4-Methoxy-N-(4-(5-(4-methoxybenzamido)benzo[d]oxazol-2-yl)phenyl)
benzamide (7f) (61%) as an off-white powder having mp >300 ꢀC.
1H-NMR (600 MHz, DMSO-d6, p.p.m.) d: 10.50 (s, 1H, N-H), 10.31
(s, 1H, N-H), 8.28 (s, 1H, Ar-H), 8.19 (d, 2H, J = 9.0 Hz, Ar-H), 7.99
(d, 2H, J = 8.4 Hz, Ar-H), 7.74 (d, 1H, J = 9.0 Hz, Ar-H), 7.64–7.69
(m, 3H, Ar-H), 7.51–7.55 (m, 2H, Ar-H), 7.20 (d, 2H, J = 8.4 Hz, Ar-
H), 7.09 (t, 2H, Ar-H), 3.92 (s, 6H, -CH3); IR (KBr, ⁄ cm): 3295 (mNH),
2932, 2837 (tCH(CH3)), 1648 (tC=O), 1605, 1505, 1478 (tC=C), 1315,
1176 (tC-N); EI-MS: m ⁄ z 494.5 [M+H]. C29H23N3O5 (493.16).
4-Methyl-N-(4-(5-(4-methylbenzamido)benzo[d]oxazol-2-yl)phenyl)ben-
zamide (7l) (67%) as an off-white powder having mp >300 ꢀC. H-
1
NMR (600 MHz, DMSO-d6, p.p.m.) d: 10.57 (s, 1H, N-H), 10.39 (s,
1H, N-H), 8.27 (s, 1H, Ar-H), 8.21 (d, 2H, J = 8.4 Hz, Ar-H), 8.05 (d,
2H, J = 9.0 Hz, Ar-H), 7.76–7.81 (m, 6H, Ar-H), 7.43–7.46 (m, 4H,
Ar-H), 2.51 (s, 6H, Ph-CH3); IR (KBr, ⁄ cm): 3282 (mNH), 2919 (tCH),
1654 (tC=O), 1592, 1500, 1478 (tC=C), 1321, 1165 (tC-N); EI-MS: m ⁄ z
462.4 [M+H]. C29H23N3O3 (461.17).
4-Tert-butyl-N-(4-(5-(4-tert-butylbenzamido)benzo[d]oxazol-2-yl)
phenyl)benzamide (7m) (57%) as an off-white powder having mp
3,4-Dichloro-N-(4-(5-(3,4-dichlorobenzamido)benzo[d]oxazol-2-yl)
phenyl)benzamide (7g) (57%) as an off-white powder having mp
1
>300 ꢀC. H-NMR (600 MHz, DMSO-d6, p.p.m.) d: 10.55 (s, 1H, N-
1
>300 ꢀC. H-NMR (600 MHz, DMSO-d6, p.p.m.) d: 10.73 (s, 1H, N-
H), 10.37 (s, 1H, N-H), 8.27 (s, 1H, Ar-H), 8.20 (d, 2H, J = 9.0 Hz,
Ar-H), 8.05 (d, 2H, J = 8.4 Hz, Ar-H), 7.92 (d, 4H, J = 8.4 Hz, Ar-H),
7.75 (s, 2H, Ar-H), 7.58 (t, 4H, Ar-H), 1.34 (s, 18H, CH3); IR (KBr,
⁄ cm): 3304 (mNH), 2961, 2868 (tCH(CH3)), 1638 (tC=O), 1592, 1500,
1479 (tC=C), 1318, 1167 (tC-N); EI-MS: m ⁄ z 546.5 [M+H]. C35H35N3O3
(545.27).
H), 10.58 (s, 1H, N-H), 8.24–8.26 (m, 3H, Ar-H), 8.22 (d, 2H,
J = 8.4 Hz, Ar-H), 8.04 (d, 2H, J = 9.0 Hz, Ar-H), 7.94–7.97 (m, 4H,
Ar-H), 7.72–7.79 (m, 6H, Ar-H); IR (KBr, ⁄ cm): 3257 (mNH), 1645
(tC=O), 1595, 1526, 1500 (tC=C), 1320, 1177 (tC-N); EI-MS: m ⁄ z 572.1
[M+H]. C27H15Cl4N3O3 (571.24).
N-(4-(5-(3,4-dimethoxybenzamido)benzo[d]oxazol-2-yl)phenyl)-3,4-dime
thoxybenzamide (7h) (47%) as a white powder having mp >300 ꢀC.
1H-NMR (600 MHz, DMSO-d6, p.p.m.) d: 10.42 (s, 1H, N-H), 10.26
(s, 1H, N-H), 8.25 (s, 1H, Ar-H), 8.21 (d, 2H, J = 8.4 Hz, Ar-H), 8.04
(d, 2H, J = 8.4 Hz, Ar-H), 7.75 (d, 1H, J = 9.0 Hz, Ar-H), 7.72 (d, 1H,
J = 8.4 Hz, Ar-H), 7.67 (d, 2H, J = 7.8 Hz, Ar-H), 7.57 (s, 2H, Ar-H),
7.12 (t, 2H, Ar-H), 3.86 (s, 12H, OCH3); IR (KBr, ⁄ cm): 3277 (mNH),
2934, 2837 (tCH), 1647 (tC=O), 1599, 1506 (tC=C), 1315, 1176 (tC-N);
EI-MS: m ⁄ z 554.5 [M+H]. C31H27N3O7 (553.18).
4-Propyl-N-(4-(5-(4-propylbenzamido)benzo[d]oxazol-2-yl)phenyl)benza
mide (7n) (63%) as an off-white powder having mp >300 ꢀC. H-
1
NMR (600 MHz, DMSO-d6, p.p.m.) d: 10.54 (s, 1H, N-H), 10.36 (s,
1H, N-H), 8.26 (s, 1H, Ar-H), 8.20 (d, 2H, J = 8.4 Hz, Ar-H), 8.05 (d,
2H, J = 8.4 Hz, Ar-H), 7.92 (d, 4H, J = 7.8 Hz, Ar-H), 7.75 (s, 2H, Ar-
H), 7.38 (t, 4H, Ar-H), 2.65 (t, 4H, Ar-CH2), 1.62–1.66 (m, 4H, CH2),
0.92 (t, 6H, CH3); IR (KBr, ⁄ cm): 3309 (mNH), 2957, 2929, 2870 (tCH),
1652 (tC=O), 1526, 1500, 1479 (tC=C), 1318, 1179 (tC-N); EI-MS: m ⁄ z
518.5 [M+H]. C33H31N3O3 (517.24).
4-Chloro-N-(4-(5-(4-chloro-2-nitrobenzamido)benzo[d]oxazol-2-yl)phe-
nyl)-2-nitrobenzamide (7i) (49%) as a light yellow powder having
mp >300 ꢀC. H-NMR (600 MHz, DMSO-d6, p.p.m.) d: 11.10 (s, 1H,
N-H), 10.92 (s, 1H, N-H), 8.31 (d, 2H, J = 7.8 Hz, Ar-H), 8.23 (d, 2H,
J = 9.0 Hz, Ar-H), 8.16 (s, 1H, J = 7.8 Hz, Ar-H), 8.01 (t, 2H, Ar-H),
7.89–7.92 (m, 4H, Ar-H), 7.79 (d, 1H, J = 9.0 Hz, Ar-H), 7.61 (d, 1H,
J = 9.0 Hz, Ar-H); IR (KBr, ⁄ cm): 3246 (mNH), 1654 (tC=O), 1534, 1350
(mNO2), 1350, 1173 (tC-N); EI-MS: m ⁄ z 592.2 [M+H]. C27H15Cl2N5O7
(591.03).
3-Fluoro-N-(4-(5-(3-fluorobenzamido)benzo[d]oxazol-2-yl)phenyl)benza
mide (7o) (64%) as an off-white powder having mp >300 ꢀC. H-
1
1
NMR (600 MHz, DMSO-d6, p.p.m.) d: 10.68 (s, 1H, N-H), 10.51 (s,
1H, N-H), 8.26 (s, 1H, Ar-H), 8.22 (d, 2H, J = 9.0 Hz, Ar-H), 8.04–
8.06 (m, 2H, Ar-H), 7.85 (d, 2H, J = 7.8 Hz, Ar-H), 7.81 (d, 2H,
J = 7.8 Hz, Ar-H), 7.78 (d, 1H, J = 9.0 Hz, Ar-H), 7.69 (d, 1H,
J = 9.0 Hz, Ar-H), 7.60–7.65 (m, 2H, Ar-H), 7.46–7.51 (m, 2H, Ar-H);
IR (KBr, ⁄ cm): 3320 (mNH), 1656 (tC=O), 1587, 1531, 1482 (tC=C),
1323, 1179 (tC-N); EI-MS: m ⁄ z 470.5 [M+H]. C27H17F2N3O3 (469.12).
N-(4-(5-benzamidobenzo[d]oxazol-2-yl)phenyl)benzamide (7j) (64%) as
an off-white powder having mp >300 ꢀC. 1H-NMR (600 MHz,
DMSO-d6, p.p.m.) d: 10.63 (s, 1H, N-H), 10.45 (s, 1H, N-H), 8.27 (d,
1H, J = 8.4 Hz, Ar-H), 8.21 (d, 2H, J = 9.0 Hz, Ar-H), 8.18 (d, 1H,
J = 9.0 Hz, Ar-H), 8.06 (d, 2H, J = 8.4 Hz, Ar-H), 8.98–8.00 (m, 5H,
Ar-H), 7.76 (d, 3H, J = 3.6 Hz, Ar-H), 7.61–7.65 (m, 3H, Ar-H), 7.72–
7.79 (m, 6H, Ar-H); IR (KBr, ⁄ cm): 3262 (mNH), 1653 (tC=O), 1533,
1493, 1410 (tC=C), 1325, 1176 (tC-N); EI-MS: m ⁄ z 434.6 [M+H].
C27H19N3O3 (433.14).
3-Chloro-N-(4-(5-(3-chlorobenzamido)benzo[d]oxazol-2-yl)phenyl)benza-
mide (7p) (42.9%) as an off-white powder having mp >300 ꢀC. H-
1
NMR (600 MHz, DMSO-d6, p.p.m.) d: 10.70 (s, 1H, N-H), 10.54 (s,
1H, N-H), 8.26 (s, 1H, Ar-H), 8.22 (d, 2H, J = 8.4 Hz, Ar-H), 8.04–
8.06 (m, 4H, Ar-H), 7.96 (d, 2H, J = 7.2 Hz, Ar-H), 7.78 (d, 1H,
J = 9.0 Hz, Ar-H), 7.74 (d, 1H, J = 9.0 Hz, Ar-H), 7.69 (t, 2H, Ar-H),
7.59–7.62 (m, 2H, Ar-H); IR (KBr, ⁄ cm): 3312 (mNH), 1651 (tC=O),
1596, 1524, 1501 (tC=C), 1324, 1178 (tC-N); EI-MS: m ⁄ z 502.2 [M+H].
C27H17Cl2N3O3 (501.06).
4-Amino-N-(4-(5-(4-aminobenzamido)benzo[d]oxazol-2-yl)phenyl)benza-
mide (7k) (44%) as a sandy beige solid having mp >300 ꢀC. 1H-
NMR (DMSO-d6, p.p.m.) 600 MHz, d: 10.12 (s, 1H, N-H), 9.46 (s,
1H, N-H), 8.22 (s, 1H, Ar-H), 8.14–8.18 (m, 3H, Ar-H), 8.02 (d, 2H,
J = 9.0 Hz, Ar-H), 7.95 (s, 1H, Ar-H), 7.83 (d, 1H, J = 9.0 Hz, Ar-H),
3-Methyl-N-(4-(5-(3-methylbenzamido)benzo[d]oxazol-2-yl)phenyl)ben-
zamide (7q) (67%) as an off-white powder having mp >300 ꢀC. H-
NMR (600 MHz, DMSO-d6, p.p.m.) d: 10.57 (s, 1H, N-H), 10.40 (s,
1H, N-H), 8.26 (s, 1H, Ar-H), 8.21 (d, 2H, J = 8.4 Hz, Ar-H), 8.05 (d,
2H, J = 9.0 Hz, Ar-H), 7.75–7.81 (m, 6H, Ar-H), 7.43–7.46 (m, 4H,
1
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Chem Biol Drug Des 2012; 79: 1018–1024